High-load, oligomeric dichlorotriazine: a versatile ROMP-derived reagent and scavenger.
A new high-load, soluble oligomeric dichlorotriazine (ODCT) reagent derived from ring-opening metathesis polymerization (ROMP) is reported as an effective coupling reagent, scavenger of nucleophilic species, and activator of DMSO for the classic Swern oxidations. Two variants of this reagent (2G)ODCT 4 and (1G)ODCT 16, possessing theoretical loads of 5.3 and 7.3 mmol/g, respectively, have been synthesized. Preparation was accomplished via simple synthetic protocols affording free flowing powders, amenable for large-scale production. Removal of the spent oligomeric reagent was achieved via either precipitation of the spent reagent or simple filtration utilizing a silica SPE, followed by solvent removal, to deliver products in excellent yield and purity. In addition, the corresponding norbornenyl monomer 3 was successfully demonstrated in a couple-ROMP-filter protocol utilizing in situ polymerization, achieving comparable results versus the corresponding oligomeric variant.
Rolfe
Alan
A
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Probst
Donald A
DA
Volp
Kelly A
KA
Omar
Iman
I
Flynn
Daniel L
DL
Hanson
Paul R
PR
D000438:Alcohols / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002713:Chlorine / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
D000438:Alcohols; D000577:Amides; D000588:Amines; D007202:Indicators and Reagents; D011108:Polymers; D014227:Triazines; D002713:Chlorine